Producción Científica Profesorado

Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products



Suárez Castillo, Oscar Rodolfo

2006

Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products. Oscar R. Suárez-Castillo, Maricruz Sánchez-Zavala, Myriam Meléndez-Rodríguez, Luis E. Castelán-Duarte, Martha S. Morales-Ríos, Pedro Joseph-Natha. http://dx.doi.org/10.1016/j.tet.2006.01.036


Abstract


This work describes a general protocol for the oxidation of indole and oxindole derivatives with dimethyldioxirane to give 3-hydroxyoxindoles present in many natural products. This strategy allowed us to synthesize the natural product 1, to carry out the first total synthesis of 4, a formal total synthesis of donaxaridine (5) and to achieve the synthesis of pyrroloindoline 8, a debromo analogue of the natural product flustraminol B (7).



Producto de Investigación




Artículos relacionados

Reactivity of TpMe2Ir(C2H4)(DMAD) with carboxylic acids. A DFT study on geometrical isomers and stru...

One-potsynthesis of conformationallyrestrictedspirooxindoles

First Total Synthesis of ()-Flustraminol B

Trapping enols of esters and lactones with diazomethane

Transesterifications mediated by t-BuNH2

Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase

Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters

Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Synthesis of Indolylindolines Mediated by tert-BuNH2